Find Hotels with Bars in Pittsfield, MA

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Check availability on Pittsfield Hotels with Bars

Our top choices for Pittsfield hotels with a bar

Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is NT$3,237
NT$3,616 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (667 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is NT$4,281
NT$4,781 total
includes taxes & fees
Mar 1 - Mar 2
Hilton Garden Inn Lenox Pittsfield
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (824 reviews)
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is NT$4,682
NT$5,230 total
includes taxes & fees
Feb 22 - Feb 23
Hotel On North
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NT$4,368
NT$4,879 total
includes taxes & fees
Mar 1 - Mar 2
Element Lenox Berkshires
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (88 reviews)
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
The price is NT$3,535
NT$3,924 total
includes taxes & fees
Feb 22 - Feb 23
Gregory House Country Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (862 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
Berkshires Untold
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is NT$2,912
NT$3,252 total
includes taxes & fees
Mar 1 - Mar 2
The Yankee, Trademark Collection by Wyndham
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (894 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is NT$2,348
NT$2,771 total
includes taxes & fees
Mar 1 - Mar 2
Cozy Corner Motel
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,004 reviews)
"Very clean and warm room, kind staff, many fresh fruits for breakfast. Wonderful stay in cold January."
United States
ALEXEI
The price is NT$2,404
NT$2,685 total
includes taxes & fees
Feb 21 - Feb 22
Willows Motel Williamstown
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (19 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is NT$6,160
NT$7,933 total
includes taxes & fees
Feb 24 - Feb 25
Prospect Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Beautiful room with a fireplace. "
Carolyn 2-night trip
Posted 12 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 74 hotels and other lodging options to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, consider a visit to Berkshire Museum and Colonial Theater.
What are the best hotels with bars in Pittsfield?
Here's some of the top Pittsfield accommodations with bars: Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hotel On North: Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Colonial Theater, and Bousquet Ski Area, and then find a cozy spot for a nightcap. Other places to see include Hancock Shaker Village and Housatonic River. Pittsfield is appreciated for its entertainment venues.
When is the best time to visit Pittsfield?
Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Pittsfield and around the area?
You might want to make the most of these transportation choices in and around Pittsfield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.

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